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バンデタニブ

バンデタニブ 化学構造式
443913-73-3
CAS番号.
443913-73-3
化学名:
バンデタニブ
别名:
バンデタニブ;バンデタニブ (JAN)
英語化学名:
Vandetanib
英語别名:
CS-97;D6474;Zactima;ZD 6474;AZD6474;Vetanib;VANDETANIB;Vandetanib base;ZD6474; ZACTIMA;ZD6474;AZD-6474
CBNumber:
CB01011762
化学式:
C22H24BrFN4O2
分子量:
475.35
MOL File:
443913-73-3.mol

バンデタニブ 物理性質

融点 :
240-2430C
沸点 :
538.2±50.0 °C(Predicted)
比重(密度) :
1.406
闪点 :
279.3℃
貯蔵温度 :
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
酸解離定数(Pka):
8.92±0.10(Predicted)
CAS データベース:
443913-73-3

安全性情報

Sフレーズ  24/25
HSコード  29333220
有毒物質データの 443913-73-3(Hazardous Substances Data)

バンデタニブ 価格

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入

バンデタニブ 化学特性,用途語,生産方法

効能

抗悪性腫瘍薬, 受容体チロシンキナーゼ阻害薬

商品名

カプレルサ (サノフィ)

説明

In April 2011, the U.S. FDA approved vandetanib (ZD6474) for the treatment of symptomatic or progressive medullary thyroid cancer (MTC) in adult patients with inoperable advanced ormetastatic disease. Vandetanib inhibits KDR/VEGFR2, VEGFR3, EGFR, and RET kinases with IC50's of 40, 110, 500, and <100 nM, respectively. In athymic mice bearing MTC tumors, a 14.5-fold reduction of tumor volume was observed after 45 days of treatment with vandetanib at 50 mg/kg/day. The decrease in tumor volume was accompanied by decreases in mitotic index (Ki67) and tumor angiogenesis in treated xenografts. Key steps in the synthesis of vandetanib include the displacement of the chlorine atom from 7-benzyloxy-4-chloro-6-methoxyquinazoline with 4-bromo-2- fluoroaniline under acidic conditions in a protic solvent and a Mitsunobu reaction of a N-protected piperidine alcohol with a phenol.

化学的特性

Yellow Solid

Originator

Astra Zeneca (United Kingdom)

使用

Vandetanib (Zactima, ZD6474) is a potent inhibitor of VEGFR2 with IC50 of 40 nM.

使用

Vandetanib (ZD6474) is a potent inhibitor of VEGFR2 with IC50 of 40 nM

使用

Vandetanib is a once-daily oral inhibitor of vascular endothelial growth factor receptor-2 and epidermal growth factor receptor kinase activity. The activity of Vandetanib plus Docetaxel was assessed in patients with previously treated non-small-cell lung cancer (NSCLC).

使用

Vandetanib is a broad spectrum, orally available kinase inhibitor that targets primarily tyrosine kinases, including vascular endothelial growth factor receptor (VEGFR) and epidermal growth factor receptor (EGFR), with IC50 values in the nanomolar range. It also potently blocks non-receptor tyrosine kinases, including ABL, RET, and SRC, as well as several serine/threonine kinases. Primarily because of its effects on receptor tyrosine kinases like VEGFR and EGFR, vandetanib inhibits angiogenesis, cell growth, and metastasis and is effective against certain forms of cancer.[Cayman Chemical]

brand name

Zactima (AstraZeneca);Caprelsa.

臨床応用

Vandetanib, an oral VEGF, EGF, and RET receptor tyrosine kinase inhibitor, was developed by AstraZeneca for the treatment of symptomatic or aggressive medullary thyroid cancer (MTC) in patients with advanced or metastatic disease. This is the first drug approved for the treatment of MTC. Trials for other cancer indications such as small-cell lung cancer (SCLC), breast cancer, head and neck cancer, colorectal cancer, hormone-resistant prostate cancer, and papillary thyroid cancer are currently being explored. While AstraZeneca had previously developed ZD-4190 which displays similar efficacy and pharmacokinetic profile to vandetanib, vandetanib exhibited significantly improved solubility.

Chemical Synthesis

Vandetanib contains a 4-anilinoquinazoline scaffold similar to other EGFR inhibitors, and the synthesis described below is based on a recent patent (Scheme).


Commercially available vanillic acid (262) was treated with benzyl bromide, DIPEA and Et3N to give ethereal ester 263 in 93% yield. Arene 263 was then subjected to nitration conditions to provide nitroarene 264 in 86% yield, which underwent immediate reduction with sodium dithionite in acetonitrile and water to give aniline 265 in 92% yield. Aniline 265 was then treated with foramidine acetate in isobutanol which affected an intramolecular cyclization reaction, giving rise to dihydroquinazolin-4-one 266 in 98% yield. Heterocycle 266 was treated with phosphorous oxychloride and the resulting quinazoline chloride was subsequently reacted with 4-bromo-2-fluoroaniline 267 and trifluoroacetic acid to give hydroxyaniline 268 in 90% for the three-step sequence. Phenolic azacycle 268 was then alkylated with sulfonate 269 to furnish piperidine 270 in 77% yield. Subsequent treatment with formic acid and aqueous formaldehyde under elevated temperatures gave vandetanib (XXIII) in 91% yield.

バンデタニブ 上流と下流の製品情報

原材料

準備製品


バンデタニブ 生産企業

Global( 308)Suppliers
名前 電話番号 ファックス番号 電子メール 国籍 製品カタログ 優位度
Jurong Coupling Biotechnology Co., Ltd.
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Nanjing Shizhou Biotechnology Co., Ltd
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Nanjing Shizhou Biotechnology Co., Ltd
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HONG KONG IPURE BIOLOGY CO.,LIMITED
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Capot Chemical Co.,Ltd.
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Henan Tianfu Chemical Co.,Ltd.
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Hangzhou FandaChem Co.,Ltd.
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Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070
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Shanghai Yingrui Biopharma Co., Ltd.
+86-21-33585366 E-mail:sales03@shyrchem.com
+86-21-34979012 sales03@shyrchem.com CHINA 739 60

443913-73-3(バンデタニブ)キーワード:


  • 443913-73-3
  • 7-((4-aminocyclohexyl)methoxy)-N-(4-bromo-2-fluorophenyl)-6-methoxyquinazolin-4-amine
  • Vandetanib(Zactima),ZD6474
  • Vandetanib(ZactiMa,AZD6474)
  • Vandetanib base
  • N-(4-BroMo-2-fluorophenyl)-6-Methoxy-7-[(1-Methylpiperidin-4-yl)Methoxy]-4-aMino-quinazoline
  • Vandetanib (ZactiMa)
  • ZD6474; ZACTIMA
  • VANDETANIB
  • 4-Quinazolinamine, N-(4-bromo-2-fluorophenyl)-6-methoxy-7-[(1-methyl-4-piperidinyl)methoxy]-
  • Vandetanib for research
  • 4-(4-Bromo-2-fluoroanilino)-6-methoxy- 7-[(1-methylpiperidin-4-yl)methoxy]quinazoline
  • N-(4-Bromo-2-fluorophenyl)-6-methoxy-7-[(1-methyl-4-piperidinyl)methoxy]-4-quinazolinamine
  • Zactima
  • ZD 6474
  • ZD6474;AZD-6474
  • Vandetanib (ZD6474, Zactima)
  • CS-97
  • Vandetanib, >=98%
  • 4-(4-Bromo-2-fluoroanilino)-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazoline Vandetanib (Zactima)
  • Vandetanib 4-(4-Bromo-2-fluoroanilino)-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazoline
  • AZD6474
  • Vandetanib(AZD6474)
  • ZD6474;ZD-6474;ZD 6474
  • D6474
  • 4-[(4-Bromo-2-fluorophenyl)amino]-6-methoxy-7-[(1-methyl-4-piperidyl)methoxy]quinazoline
  • Vandetanib fandachem
  • Vandetanib USP/EP/BP
  • Vetanib
  • バンデタニブ
  • バンデタニブ (JAN)
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